Pyridine → HCID 15281426, compound

HRID 2209833Notes

Reaction equation

HRID 2209833 reaction equation
C1(CC([NH:10][C@@H:11]2[C:50](=[O:51])[N:13]3[C:14]([C:34]([O:36][CH:37]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:35])=[C:15]([C:18]4[CH:19]=[CH:20][C:21]5[C:22](=[O:33])[C:23]6[C:28]([C:29]=5[CH:30]=4)=[CH:27][CH:26]=[C:25]([CH2:31]O)[CH:24]=6)[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:59].OP([O-])(O)=O.[K+]>C(Cl)Cl.CO>[NH2:10][C@@H:11]1[C:50](=[O:51])[N:13]2[C:14]([C:34]([O:36][CH:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[C:22](=[O:33])[C:23]5[C:28]([C:29]=4[CH:30]=3)=[CH:27][CH:26]=[C:25]([CH2:31][Cl:59])[CH:24]=5)[CH2:16][S:17][C@H:12]12

Participants

7

Reactant 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 516951Monobasic potassium phosphateHCID 15378845HCID 15378845, compound

Product 1

HCID 15281426HCID 15281426, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Benzhydryl 7β-phenylacetamido-3-(7-hydroxymethyl-9-fluorenon-3-yl)-ceph-3-em-4-carboxylate (150 mg) was dissolved in methylene chloride (6 ml), cooled to -15° under nitrogen. Pyridine (0.240 ml was added followed by PCl5 (2.4 ml, 8% solution in CH2Cl2). The reaction mixture was stirred at -15° to -10° for 65 min. The temperature was then lowered to -300 and MeOH (1.5 ml) was added drop wise and the reaction was stirred at -10° to -5° for 1.5 hrs, then at 0° for 1 hr. and then at room temperature for 1 hr. KH2PO4 (6.0 ml, 0.5M solution) was added. The reaction mixture was stirred vigorously for 0.5 hr. The organic solvents were removed under reduced pressure and the residual suspension was filtered, the residue was washed well with water and then with ether and the residue dried to give the desired product as a yellow solid (108.3 mg).

Workup

  1. temperaturecooled to -15° under nitrogen
  2. additionwas added drop wise
  3. stirringthe reaction was stirred at -10° to -5° for 1.5 hrs
  4. waitat 0° for 1 hr
  5. waitand then at room temperature for 1 hr
  6. stirringThe reaction mixture was stirred vigorously for 0.5 hr
  7. customThe organic solvents were removed under reduced pressure
  8. filtrationthe residual suspension was filtered
  9. washthe residue was washed well with water
  10. dry with materialwith ether and the residue dried

Sources & evidence

ORD record
ord-93ce3f470e92493ba7382a9ea9749311
Source dataset
uspto-grants-1995_10
Patent number
US05455239

Reaction notes

Loading…